Tuscany & Umbria (trip)

Tuscany & Umbria

  • Siena Airport, Sienna, Italy
  • Active & Adventure
Italy, Europe

from $3,995* per person7 DaysJune, September
Boutique accommodations Exertion level: 5
Operator: The Wayfarers 16 people max
If Tuscany is a legend, Umbria is a little-known medieval fable, its green heart beating in the shadow of its more famous neighbor. Our Walk combines the Tuscan hills, vineyards and Renaissance cities with a journey through the bucolic landscapes and enchanting lakes of Umbria.

We traverse a romantic landscape of mountains, rolling hills and deep valleys; walking on white roads that dip between hilltop towns, or shady forest tracks.

We savor private tastings of Chianti and Sagrantino wine, olive oil and honey, explore the glories of Siena, Assisi and Orvieto, discover awe-inspiring frescoes and visit the hill-top treasures of Cortona and Montefalco.

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Locations visited/nearby

Italy, Europe

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Itinerary

Sunday

We rendezvous in Siena for a short walking tour of this gem of Italian cities. We wonder at the stunning gothic Cathedral, dedicated to St. Mary of the Assumption and decorated in white and black marble to signify the black and white horses of Senius and Aschius, the city's founders. We visit the Town Hall and have an expresso in the breathtaking Piazza del Campo. We drive to our hotel in Radda in Chianti, in the midst of the beautiful countryside, for an Introductory Talk and Welcome Dinner.
Overnight: Radda in Chianti

Monday

Our walk today centres on the Strada Chiantigiana as it meanders to and fro through classic Tuscan countryside and we cross the vineyards that make the Chianti region renowned for its wine. As we approach Monteriggioni, we admire the 13th-century walls complete with fourteen towers, and we lunch here in this romantic medieval village, once a Sienese fortress. We return to our hotel along country tracks, through ancient farmsteads, always in the shade of the famous cypress and pine trees that are such a feature of a Tuscan landscape.
Overnight: Radda in Chianti

Tuesday

After a short transfer, we walk to famed Badia a Coltibuono, through a forest whose first trees were planted by the Benedictines in the 11th century. We enjoy a private visit of the house, cellars and gardens and a tasting of the olive oils and honey produced here. We lunch in the village of Gaiole and walk on, along ancient hunting tracks in glorious countryside of vineyards and castles, to meet the van for the transfer to Cortona in time for dinner.
Overnight: Cortona

Wednesday

This morning in Cortona, we walk around the medieval ramparts of this ancient Etruscan city clinging to the hillside; a town already old when its lands were wasted by Hannibal. We wander the steep, narrow streets paved with flagstones and come across surprising arcaded squares, alleyways, churches and gardens. We pass by 'Bramasole' the house made famous by Frances Mayes in her book 'Under the Tuscan Sun'.  For the rest of the morning options abound;  we may take some time out for shopping, walk the stations of the cross, or visit the Etruscan or Diocesan museums with superb painting from the Sienes school.  After lunch, our walk takes us to the monastery where St Francis made his will - and we return to Cortona.
Overnight: Cortona

Thursday

An early start to the pastures and pine forests of Monte Subasio - a plateau with views to Spoleto Vale - then a slow descent along a spur of the mountain before reaching the terraced slopes of Assisi. Elegant squares and the Basilica of St. Francis are the pivot of this exceptional town and its architectural splendors. Our walk ends at the Basilica before  we continue to lovely Montefalco and our beautiful villa hotel just outside the walls.
Overnight: Montefalco

Friday

Today, along rustic byways and through the olive groves, we explore the vineyards of the renowned Sagrantino and rosso di Montefalco to reach Bevagna, an ancient town of Romanesque churches and the remains of Roman architecture. After a medieval lunch where we sample authentic fare and dress the part, we return to Montefalco for a wine-tasting and Farewell Dinner.
Overnight: Montefalco

Saturday

After breakfast, we leave for Orvieto. Here we have time to explore this stunning Etruscan city, visiting its cathedral and looking round the famous labryinth of caves carved out of the volcanic rock under the city and used as cellars, shelters and protection against seiges for hundreds of years.  We say 'arrivederci' at the rail-station.

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